Dating Advice from Philosophers

Public domain

Niccolo Machiavelli

Dear Machiavelli,

My friends want to throw me a bachelor party. Knowing them, it will involve strippers, booze, drugs, the works. I promised my fiancée I would stay away from that kind of stuff, but I’m really tempted to go, and I’d hate to let the guys down. What should I do?



My Liege,

I am unsure how to advise you in this instance, for your status in this world has much bearing on the matter. Are you a common man, or are you a prince? For it is well known that those actions which are considered most virtuous in a common man are in fact a vice in a prince, and that which would be vice for the lowest laborer is in fact raised to holy virtue when undertaken by a prince. Be you of the lower classes, stay true to your course and all will be well. Be you my liege, I pray you, indulge yourself.

Public domain (ironic, isn’t it?)

Adam Smith

Dear Adam Smith,

I’m meeting a girl for a first date, and I’m not sure what I should bring. I know tradition calls for flowers and chocolates, but do modern ladies still go for that sort of thing? Or would I just come across old fashioned?


Lonely and Confused

Dear Consumer,

The women of this age are as they have always been and as they shall always be, a part of the broader tapestry of our economic fabric. To deny that is to deny the truth of what makes all nations mighty. If you would impress and woo the lady, I would suggest you show her that you care for your nation by supporting the lifeblood of the nation: commerce. Support the florist, the chocolatier, yea, even the dressmaker and the milliner. In this way you shall prove you are a great philanthropist as well as a mighty provider.

Public domain

Friedrich Nietzsche

Dear Nietzsche,

My girlfriend and I have been together for over two years, and we love each other very much. I’m thinking about proposing, but there’s just one problem. Ever since she was a little girl, she’s had this dream of a big church wedding. I’m agnostic, and both of my parents are atheists. I just don’t see that working out. Can you help?


In Love but Not In Church

Dear Superman,

Ah, women. They make the highs higher and the lows more frequent. Every church is a stone on the grave of a god-man: it does not want him to rise up again under any circumstances. Is life not a thousand times too short for us to bore ourselves? It is not a lack of love, but a lack of friendship that makes unhappy marriages. Love is blind; friendship closes its eyes.

What I’m saying here is just rent out the local VFW Hall.

© Marie-Lan Nguyen / Wikimedia Commons


Dear Plato,

My boyfriend cheated on me a few months ago, and I just can’t seem to let it go. I still care about him, but I can’t get past this, and it is ruining our relationship. Should I forgive him or should I move on?



Dear Prisoner,

What you fail to understand is that your concerns are not real. They are simply the shadows of old wounds that you cling to out of fear of losing the illusions you have lived with all your life. Throw off the shackles of your fear, and acknowledge that which torments you is naught but a specter cast by the flickering light of a neon vacancy sign. Do not turn your anger on those who would drag you into the light of truth, but rather on the one who has in truth earned it, and kick him to the curb.

Like the sun, wind, and water, this photo is public domain.


Dear Laozi,

I feel as though my life has been spiraling out of control lately, and I just don’t know what to do. I am looking for some sense of balance, but I can’t abandon my wife to withdraw from society and meditate in nature for a lifetime. Is there some weekend course I can take to achieve enlightenment quickly?


Seeker of Truth

Dear Ineffable One,

While in days past the search for the Tao could take a lifetime, modern society no longer has the proper respect for the venerable sage. Where the strongest oak will break in a hurricane, the supple reed will simply bend. So too does the Eternal Tao adapt to change. If you seek to understand the Way, simply wear an outfit from JCPenney while eating a sandwich from Chick-Fil-A. In this way you will know balance.

© 663highland / GNU Free Documentation License v. 1.2

Sun Tzu

Dear Sun Tzu,

My name is Jenny and I am eight years old and there’s a boy I really like and I don’t know if he likes me back and I don’t know how to ask him if he likes me and I was wondering if you could tell me how I should ask him. Thank you very much for you help.

Your freind,


Dear Jen Ni,

The strong warrior charges in like an ox; the wise warrior is subtle and flows like water. To gauge your opponent’s intentions, send your most trusted lieutenant forward on a scouting mission to determine where he lies. If conditions seem favorable, I would suggest you send a missive of alliance, stating your intentions indirectly yet plainly, constraining your opponent’s choices to those that you would find most favorable: “Do you like me? Yes_ Very Much_”

For more, check out “Dating Advice From Historical Figures“, “Dating Advice From Mythological Creatures“, and “Dating Advice From Classical Deities“.


Don’t Hate the Player, Hate the Played

I’ve already given guys a blast of bile for their pathetic attempts at making women the source of their perpetual dating woes, so I feel it’s only fair that I turn the petty hate machine (dodged that copyright bullet!) on the gentler sex. One of the biggest issues I have with women, and this is not all women but a significant enough minority to be worth mentioning, is the ones who engage in the following pattern:

  • Date “the wrong guy”.
  • Insist on making an issue out of it/complaining about it. Loudly.
  • Go back to him for more. Repeatedly.
  • Finally break up with him.
  • Rinse and repeat.

“How do I always find myself in this position?” is a refrain I have often heard. Let me answer that bluntly: by opening your eyes after you have already put yourself in that position. No, I’m not trying to blame the victim here, I’m trying to get everybody, men and women alike, to start taking responsibility for the choices they make and the consequences of those choices. Let me play Jacob Marley for a moment and introduce you to the Ghosts of Your Choices Past, Present, and Future. They may help shed some light on the reasons you end up reliving the same “relationships” over and over.

Going to clubs and bars to meet men. I’ve heard that women go to clubs to dance and have a good time. This is a foreign concept to me and every straight man in existence (I can’t speak for the gay men, although the ones I have known generally favored clubbing as a means of picking up guys as well.) That’s the first strike against meeting someone at a club; you’re there for two completely different reasons. You may want to meet someone to hang out with; he’s there to meet someone to hook up with. Even if you are both interested in more than a one night – if that – stand, consider the environment of a club. It’s crowded, loud, dark except for the flashing lights, and oh yeah, you and everybody else is likely to be drunk. So your expectation is that… he’s going to be charmed by your rapier wit? The depth of your knowledge on the Crimean War? Or the tattoo of Mickey Mouse on your thigh? Speaking of which…

Dressing like a whore. Dave Chappelle covered this one already in Killin’Them Softly, so I’m just going to quote him verbatim: “The girl says ‘Oh uh-uh, wait a minute! Wait a minute! Just because I’m dressed this way does not make me a whore!’ Which is true. Gentlemen, that is true. Just because they dress a certain way doesn’t mean they are a certain way. Don’t ever forget it. But ladies, you must understand that is fucking confusing. It just is. Now that would be like me, Dave Chappelle, the comedian, walking down the street in a cop uniform. Somebody might run up on me, saying, ‘Oh, thank God. Officer, help us! Come on. They’re over here. Help us!’ ‘Oh-hoh! Just because I’m dressed this way does not make me a police officer!’ See what I mean? All right, ladies, fine. You are not a whore. But you are wearing a whore’s uniform.”

Showing no respect for yourself. This goes well beyond where you go or how you dress. This goes into how you approach your entire life. Simply put, when 90% of your time in a given situation is misery, and you stay in that situation, you are not respecting yourself. I don’t care if this is a relationship, a job, a housing situation, time with a “friend” (why do we even need the term “frienemy” anyway?), or anything else. No, life is not perfect, and sometimes you have to suck it up. But just because 10% is great does not justify the other 90% being misery. Stand up for yourself, treat yourself right, and don’t let others treat you differently.

Showing no respect for the men you date. Ever wonder why you can’t keep a good man? Take a look at the way you treat them. There are women who take advantage of men, use them as walking credit cards, ignore their emotional needs, dump on them all the time, screech at them and deride them. My favorite is the physical abuse double standard. “Gentlemen don’t hit ladies.” “It was just a little tap.” “Oh, get over it you big baby.”  And then they wonder why he left. Here’s a hint: spend one day letting a guy treat you the way you treated him. Be honest. See if you can make it a full twenty-four.

At the end of the day, you picked them. Here’s a hint: if you have ever uttered the words “you’re a nice guy, but…” to a guy who has asked you out, you are part of the problem, not the solution, and I’ll tell you why. Option one is you lied to him. He’s not a nice guy, you would never date him, and in fact you are looking for someone to recue you at this moment. Unless you are in fear for your physical health, this is a cheap cop-out. Option two is that you do mean it, he is a nice guy, but you just can’t see yourself dating him. But then you really don’t have a good answer for the follow-up question; you think you do, but you don’t, because you ask the same question yourself in a different form all the time.

Here’s that question, and you need to think about it in solitude, when you’re not under emotional pressure from some guy trying to hook up with you: “Why?” Why can’t you see yourself dating him? You just admitted he’s a nice guy. Or to flip it around, you so often ask “Why can’t I find a nice guy to date?” There he is. He came to you, and you turned him away. But you said yes, time and again, to the guy who was bad to you and for you.

Life is not simply what happens to us as we are passive recipients; life is the result of our active choices. As Geddy Lee sang, “If you choose not to decide, you still have made a choice.” Your love life is the same way. It does not happen to you; it is the accumulation of the choices you have made, and will continue to be exactly that. When you want to have something better, you will need to make it for yourself, or at the very least recognize it when it comes along.

John Cusack You Ain’t

Today I want to reach out to the lonely guys. The ones who sit by themselves, pining away for the perfect girl who just hasn’t noticed how perfectly perfect he is for her, and one day they will live a perfectly perfect life together that will be just perfect. You know who you are. Chances are you think you’re this girl’s best friend; hell, she’s even told you so on more than one occasion. It just kills you a little more inside each time she does, but that’s okay, because someday she’ll see the real you, and dump that asshole boyfriend she keeps going back to. Yeah, it’s gonna happen. Any day now.

I’m here to tell you some truths you need to hear, some things you may not have heard before or maybe you have, but I say them in a way you haven’t heard them before: I say them with love in my heart, because I was you, once upon a time. Yes, my friends, I was that guy. If you don’t believe me I can provide more than a few character witnesses, but suffice to say I had my angsty teenage moments that stretched into years, and I finally found the cure.

Here’s what I want you to do: put down the half-caff latte. Step away from the copy of “Say Anything”. Drop the composition notebook full of shitty love poetry that you refuse to show to anyone anyway because “they just don’t understand you”. Understand this: you are not John Cusack, and life is not a romantic comedy. Two hours from now you will still be lonely, she will still be with him, and nothing will be different.

Now here are some of the unhelpful things you may be used to hearing, along with the typical responses (which happen internally more often than not):

Them: “You just need to be yourself.”

You: “Who else am I?”

Them: “You just need some confidence.”

You: “How am I supposed to do that?”

Them: “You’ll find the right girl… eventually.”

You: “When?”

I’m going to address these one at a time, as they are generally a mix of (as you have guessed by now) hopeful optimism and outright deception. Let’s start from the top. First off, who you need to be depends on what you want. If you keep getting rejected time and again by women, maybe “being yourself” shouldn’t be the top of your priority list. Instead, consider being somebody else. For instance, consider being someone who doesn’t come across as creepy. Also, being someone who has a job, doesn’t live with his parents, owns a car, understands basic hygiene, and has some concept of social graces can do wonders for you. Assuming you already have all of these going for you, you can move on to the next item on the list.

Confidence. Ah, that old canard. Maybe the problem isn’t confidence but communication skills. Here’s a phrase to practice while looking in the mirror: “Yes, actually.” Use this phrase the next time the girl who thinks you’re “best friends” asks something like “Are you asking me out?” or “Did you think this was a date?” or “Wait, are you straight?” You’ll be amazed at how quickly it will change the dynamic of your relationship. Most of the time it will end your relationship, but at least you will be confident about where you stand on getting a date with her. Ever. Oh, and while you’re looking in the mirror, how about comparing your wardrobe to that “asshole” she’s dating? Is he wearing the same kind of clothes now that he was wearing in the seventh grade? Are you? If the answer to one of those questions was “yes”, I bet I can guess which one. (Unless he’s a hipster. If she’s dating a hipster she deserves him.)

Finally, you’ll meet the right girl when you stop chasing after the wrong ones. Everybody has heard that women can smell desperation, but nobody has any idea what that means. Well, lucky you, I’m going to give you a little hint. WOMEN ARE NOT STUPID. If a woman sees you panting after every other woman around and asking them all out, getting shot down by each in turn before you deign to ask her out, do you really think she’s going to be grateful you finally got around to her? Conversely, if you hang on her every word, doing everything she asks of you all the time in the hopes she may grace you with just a morsel of her attention, why should she give a damn about you?

So what do all these things have in common? Respect. Respect for yourself, and respect for the woman you want to have in your life. When you respect yourself enough to hold yourself to that higher standard, others will see it and want you for who you are. When you respect others enough to clearly communicate your wants and needs without being needy and without treating them like objects or simply placeholders, you come across as confident. And when you see women as intelligent partners in meaningful relationships, not simple conquests or objects of worship, the right girl will find you.

Mine did.